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Consider popping a few of these questions on your next first date and see where they lead the conversation. What do they wish they could have done differently, if anything? You don’t have to rapid fire interrogate someone, of course, but it can lead to a conversation about their past that’s meaningful but still light. This isn’t meant to prompt a confession of your date’s failures. What about you, what do you wish you were better at? This question will let your date show their vulnerable side, and admit to something they’re not entirely comfortable with, particularly if you chip in first to show solidarity.